Enantioselective total synthesis of macrolide (+)-neopeltolide
Arun K Ghosh1, Khriesto A Shurrush, Zachary L Dawson
1Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana, USA. akghosh@purdue.edu.
Abstract:
The asymmetric total synthesis of the anti-proliferative macrolide (+)-neopeltolide has been completed. The stereochemically defined trisubstituted tetrahydropyran ring was constructed via a catalytic hetero-Diels-Alder reaction creating two new chiral centers in a highly diastereoselective manner. The other key features of this synthesis included Brown's asymmetric allylation to install the requisite C-11 and C-13 stereocenters. The synthesis of the oxazole side chain consisted of a hydrozirconation of an alkynyl stannane to establish the Z stereochemistry, followed by a palladium catalyzed cross coupling to introduce the desired Z olefin in the oxazole side chain.
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